(3aS,7R,7aS)-7-Hydroxy-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione | 736151-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aS,7R,7aS)-7-Hydroxy-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione
• 英文别名: (3aS,7R,7aS)-7-hydroxy-1-(4-methoxyphenyl)-5-[(4-methoxyphenyl)methyl]-3a,6,7,7a-tetrahydro-3H-imidazo[4,5-c]pyridine-2,4-dione
• CAS: 736151-90-9
• 化学式: C₂₁H₂₃N₃O₅
• 分子量: 397.431
• InChiKey: QYHUXFMFFDECOS-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (3aS,7R,7aS)-7-Hydroxy-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,7R,7aS)-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-2,4-dioxo-octahydro-imidazo[4,5-c]pyridin-7-yl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions

  摘要：

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

  DOI：

  10.1021/ol049215u
• 作为产物：
  描述：

  4-tert-butyl 5-ethyl (4S,5S)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4,5-dicarboxylate 在 platinum(IV) oxide 甲酸 、 氢气 、 二异丁基氢化铝 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 47.0h， 生成 (3aS,7R,7aS)-7-Hydroxy-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions

  摘要：

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

  DOI：

  10.1021/ol049215u

文献信息

• Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions
  作者：Takashi Ooi、Minoru Kameda、Jun-ichi Fujii、Keiji Maruoka

  DOI：10.1021/ol049215u

  日期：2004.7.1

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.